Sodium Hydroxide → 6-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(methylsulfonyl)hexanoic acid

HRID 2190199Notes

Reaction equation

HRID 2190199 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]3[C:31]([C:32](=[O:35])[NH:33][CH3:34])=[C:30]([C:36]4[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=4)[O:29][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([S:25]([CH3:28])(=[O:27])=[O:26])[C:20]([O:22]CC)=[O:21])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[CH:1]1([C:4]2[CH:5]=[C:6]3[C:31]([C:32](=[O:35])[NH:33][CH3:34])=[C:30]([C:36]4[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=4)[O:29][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([S:25]([CH3:28])(=[O:27])=[O:26])[C:20]([OH:22])=[O:21])[S:11]([CH3:14])(=[O:12])=[O:13])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58052450ethyl 6-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(methylsulfonyl)hexanoate

Product 1

HCID 580525536-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(methylsulfonyl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethyl 6-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(methylsulfonyl)hexanoate was added 1 mL 50% NaOH and 3 mL EtOH. Stirred at RT ON Removed organic solvent on vac. Added 10 mL EtOAc. Added 20 mL conc. NH4OH and 5 mL 1N HCl and extracted with EtOAc. Washed with brine. Dried over Na2SO4, and conc. on vac. To give 6-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-(methylsulfonyl)hexanoic acid.

Workup

  1. customON Removed organic solvent on vac
  2. additionAdded 10 mL EtOAc
  3. additionAdded 20 mL conc. NH4OH and 5 mL 1N HCl
  4. extractionextracted with EtOAc
  5. washWashed with brine
  6. dry with materialDried over Na2SO4

Sources & evidence

ORD record
ord-1546c0fd626240f49324010cc1c4f5da
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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